Q&A: Robert Caldwell, Owner of Caldwell Cigar Co.

Q&A: Robert Caldwell, Owner of Caldwell Cigar Co.

  • Stephen Tabak

Robert Caldwell is the face of Caldwell Cigar Co., a company founded in 2014 that produces its core line of cigars at Tabacalera William Ventura in the Dominican Republic. Caldwell entered the cigar industry in 2008, when he launched a a concierge-like service that provides cigars and cigar accessories to high-end hotels and restaurants. Today, his portfolio boasts over 10 brands made in three different countries, and he’s known for his popular collaborative blending projects with other cigarmakers. Caldwell recently sat down with assistant editor David Clough to talk about his company’s past, recent collaborations and future goals.

Clough: How did you get started in the cigar industry?
Caldwell: I was around 26 or 27 years old and I went out to eat on my birthday, and I leave my cigars in the car. Rather than going back to the car, I asked the waiter, “What cigars do you have?” This was Smith & Wollensky’s in Miami Beach—and they were sold out of everything and the humidor was a mess. I think, “I’m going to find these guys a company that does hotel and restaurant distribution, so they can actually have a proper humidor.” I Googled it, and there was nothing, so I ended up starting a company that sells cigars to restaurants and hotels. We write you the cigar menu, do the training for the staff, this and that.

Q: How did you go from Hotel Humidor to partnering with Christian Eiroa and making cigars?
A: I was continuing to build the business and I went to Wynwood with the idea of opening an office or a warehouse—something for Hotel Humidor. I was very good friends with Christian Eiroa. So we were talking and he says, ‘Why don’t you put a factory here?’ He has this idea, I have this idea, we build this idea together—Wynwood Cigar Factory. It took seven months to get the factory open. We were producing and selling about 25,000 cigars a month out of Miami with retail prices from $12 to $15. We were selling a lot of cigars, and we had a constant back order of 30,000 or 40,000 cigars.
Q: How many pairs of rollers did you have at Wynwood?
A: We had six pairs. All of them brought from Honduras on artistic visas.

Q: What made the factory successful?
A: The concept there was roll, pack, ship. So you make a cigar, it gets packaged and shipped the same day. We would produce from 8 a.m. to 2 p.m. At 2 p.m. FedEx comes—and we’d overnight all over the country. Retailers get fresh cigars the very next day. And we blended using a mixture of Honduran Corojo, Nicaraguan Habano and Peruvian Pelo de Oro tobacco. The Corojo was so sweet that it overcompensated for any bitterness or harshness that you’d have off a fresh cigar. You had a fresh-rolled experience for like 30 days, where the cigar was maybe going through a weird phase, but you didn’t taste it. So you could buy [a box of cigars], smoke half of it and kind of age it yourself. It was a really cool concept.
Q: The Wynwood factory didn’t stay open very long. What happened?
A: Unfortunately, Christian and I had two very different visions for what the brand was, and what the brand meant in terms of everything.
Q: How long did the relationship at Wynwood last?
A: The total relationship was about 16 months.  

Q: What happened next?
A: I left Wynwood and I was talking to Hernando [Caicedo, Caldwell’s business partner at Caldwell Cigar Co.] and I said to him, “Let’s start fresh with my concepts and do it a different way.” So we go down to the Dominican Republic and I had been introduced to William Ventura. He owns a factory, and they were producing amazing cigars and doing private label work. 
Q: What year did you launch Caldwell Cigar Co.?
A: It was the beginning of 2014. ...Our first [IPCPR] trade show was that summer. ... Our goal was to sell 20,000 cigars. We went in terrified, because we had originally planned not to attend the show. And we sold around 80,000 cigars—four times what our goal was.
Q: What was the allure of your products?
A: We launched our brands with a very different approach. A refined, artistic, fresh kind of agenda in terms of our packaging. And we have energy—an energy that gets people interested. We were having fun.



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